Bis(2,2′,2′′-nitrilo­triethanol)cobalt(II) bis­(acetate)

The title compound, [Co(C₆H₁₅NO₃)₂](CH₃CO₂)₂, contains two triethanol­amine ligands bound to a Co²⁺ metal centre, which lies on a crystallographic inversion site such that the asymmetric unit contains half of the cation and one acetate anion. The triethano­lamine ligands coordinate via each axial N and two of the three O atoms, while the third arm of the ligand is pendant with the hydroxyl group pointing away from the metal centre. The acetate anions are hydrogen bonded to the coordinated hydroxyl groups and also to the free arm, forming a two-dimensional sheet-like motif.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.029
• wR factor = 0.084
• Data-to-parameter ratio = 19.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Co1    -   O2      ..       5.43 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Co1    -   O3      ..       7.07 su
PLAT755_ALERT_4_C D-H     Calc     0.84000, Rep     0.84(2) ......  Senseless su
              O1   -H1      1.555   1.555
PLAT756_ALERT_4_C H...A   Calc     1.89000, Rep     1.89(2) ......  Senseless su
              H1   -O4      1.555   8.556
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C2 H3 O2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

Author Response: Two authors, Peter Turner and Jack Clegg, were involved in the crystallography. Cindy Aquino and Matija Burger synthesised the compound, Anthony Ward grew the crystals; Anthony Masters and Thomas Maschmeyer, are supervisors of the above and were involved in the intellectual input,particularly in the editing and writing of the paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

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Computing details

Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT and XPREP (Siemens, 1995); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997), WinGX32 (Farrugia, 1999), POV-RAY 3.5 (Cason, 2002) and WebLab ViewerPro 3.7 (Molecular Simulations, 2000); software used to prepare material for publication: enCIFer 1.0 (Allen et al., 2004).

Bis(2,2',2''-nitrilotriethanol)cobalt(II) bis(acetate)

Crystal data

[Co(C6H15NO3)2](C2H3O2)2	F(000) = 1012
Mr = 475.4	Dx = 1.440 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 9710 reflections
a = 14.847 (2) Å	θ = 2.6–28.3°
b = 9.5480 (11) Å	µ = 0.84 mm^−1
c = 15.473 (2) Å	T = 150 K
V = 2193.4 (4) Å^3	Prism, orange
Z = 4	0.54 × 0.48 × 0.19 mm

Data collection

Siemens SMART 1000 CCD diffractometer	2710 independent reflections
Radiation source: sealed tube	2314 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
ω scans	θmax = 28.3°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	h = −19→19
Tmin = 0.701, Tmax = 0.853	k = −12→12
20387 measured reflections	l = −20→20

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.084	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0425P)^2 + 1.1747P] where P = (Fo^2 + 2Fc^2)/3
2710 reflections	(Δ/σ)max < 0.001
141 parameters	Δρmax = 0.67 e Å^−3
0 restraints	Δρmin = −0.37 e Å^−3

Special details

Experimental. The crystal was coated in Exxon Paratone N hydrocarbon oil and mounted on a thin mohair fibre attached to a copper pin. Upon mounting on the diffractometer, the crystal was quenched to 150(K) under a cold nitrogen gas stream supplied by an Oxford Cryosystems Cryostream and data were collected at this temperature. 226 standard reflections were obtained by recollecting the first 50 CCD frames at the end of data collection. They were then used for a decay correction, giving an overall decay of 0.31%.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	−0.11174 (9)	−0.23699 (15)	0.06896 (9)	0.0243 (3)
H1A	−0.1623	−0.1794	0.0472	0.029*
H1B	−0.0942	−0.1986	0.1260	0.029*
C2	−0.14617 (10)	−0.38526 (16)	0.08256 (10)	0.0289 (3)
H2A	−0.2055	−0.3812	0.1116	0.035*
H2B	−0.1548	−0.4304	0.0256	0.035*
C3	0.04765 (9)	−0.28785 (15)	0.04447 (10)	0.0256 (3)
H3A	0.0431	−0.3902	0.0353	0.031*
H3B	0.0507	−0.2708	0.1075	0.031*
C4	0.13342 (9)	−0.23440 (15)	0.00251 (10)	0.0265 (3)
H4A	0.1861	−0.2615	0.0380	0.032*
H4B	0.1404	−0.2771	−0.0554	0.032*
C5	−0.05798 (10)	−0.26716 (15)	−0.07977 (9)	0.0259 (3)
H5A	−0.1239	−0.2585	−0.0880	0.031*
H5B	−0.0419	−0.3673	−0.0858	0.031*
C6	−0.00993 (10)	−0.18342 (16)	−0.14967 (10)	0.0280 (3)
H6A	0.0543	−0.2112	−0.1519	0.034*
H6B	−0.0373	−0.2042	−0.2066	0.034*
C7	−0.31734 (12)	−0.0327 (3)	−0.23504 (13)	0.0598 (6)
H7A	−0.3131	0.0219	−0.2885	0.090*
H7B	−0.3734	−0.0091	−0.2049	0.090*
H7C	−0.3170	−0.1329	−0.2490	0.090*
C8	−0.23776 (10)	0.00093 (17)	−0.17742 (10)	0.0311 (3)
N1	−0.03419 (8)	−0.21894 (12)	0.00897 (7)	0.0202 (2)
O1	−0.08663 (8)	−0.46875 (12)	0.13305 (7)	0.0340 (3)
H1	−0.1121	−0.4912	0.1795	0.051*
O2	0.12974 (6)	−0.08424 (11)	−0.00536 (6)	0.0222 (2)
H2	0.1679 (13)	−0.052 (2)	0.0302 (13)	0.033*
O3	−0.01653 (7)	−0.03622 (11)	−0.13230 (7)	0.0234 (2)
H3	−0.0632 (15)	−0.0083 (18)	−0.1556 (14)	0.035*
O4	−0.16334 (8)	0.03433 (14)	−0.21224 (7)	0.0375 (3)
O5	−0.24945 (8)	−0.01080 (12)	−0.09810 (7)	0.0314 (2)
Co1	0.0000	0.0000	0.0000	0.01762 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0200 (6)	0.0259 (7)	0.0269 (7)	0.0009 (5)	0.0033 (5)	0.0017 (5)
C2	0.0260 (7)	0.0297 (7)	0.0308 (7)	−0.0048 (6)	0.0009 (6)	0.0067 (6)
C3	0.0208 (6)	0.0214 (6)	0.0345 (7)	0.0021 (5)	−0.0012 (5)	0.0039 (6)
C4	0.0201 (6)	0.0202 (7)	0.0392 (8)	0.0025 (5)	0.0011 (5)	−0.0006 (5)
C5	0.0295 (7)	0.0218 (6)	0.0265 (7)	−0.0037 (5)	−0.0006 (5)	−0.0039 (5)
C6	0.0331 (7)	0.0263 (7)	0.0245 (7)	0.0005 (6)	0.0038 (6)	−0.0043 (6)
C7	0.0292 (9)	0.116 (2)	0.0342 (10)	0.0033 (10)	−0.0064 (7)	−0.0147 (11)
C8	0.0233 (7)	0.0430 (9)	0.0271 (7)	0.0065 (6)	−0.0026 (6)	−0.0063 (6)
N1	0.0171 (5)	0.0206 (6)	0.0230 (5)	−0.0009 (4)	0.0007 (4)	−0.0006 (4)
O1	0.0333 (6)	0.0363 (6)	0.0323 (6)	0.0052 (5)	0.0077 (5)	0.0121 (5)
O2	0.0176 (4)	0.0202 (5)	0.0289 (5)	−0.0004 (4)	−0.0018 (4)	−0.0006 (4)
O3	0.0233 (4)	0.0234 (5)	0.0234 (5)	0.0001 (4)	−0.0010 (4)	−0.0008 (4)
O4	0.0281 (5)	0.0604 (8)	0.0239 (5)	0.0018 (5)	−0.0001 (4)	−0.0009 (5)
O5	0.0256 (5)	0.0430 (6)	0.0257 (5)	−0.0056 (4)	−0.0010 (4)	−0.0044 (4)
Co1	0.01531 (14)	0.01765 (15)	0.01989 (15)	−0.00003 (8)	−0.00040 (8)	−0.00091 (9)

Geometric parameters (Å, º)

C1—N1	1.4889 (17)	C6—O3	1.4342 (18)
C1—C2	1.520 (2)	C6—H6A	0.9900
C1—H1A	0.9900	C6—H6B	0.9900
C1—H1B	0.9900	C7—C8	1.515 (2)
C2—O1	1.4238 (18)	C7—H7A	0.9800
C2—H2A	0.9900	C7—H7B	0.9800
C2—H2B	0.9900	C7—H7C	0.9800
C3—N1	1.4869 (17)	C8—O5	1.2445 (19)
C3—C4	1.5177 (19)	C8—O4	1.2700 (19)
C3—H3A	0.9900	N1—Co1	2.1557 (12)
C3—H3B	0.9900	O1—H1	0.8400
C4—O2	1.4399 (17)	O2—Co1	2.0890 (10)
C4—H4A	0.9900	O2—H2	0.85 (2)
C4—H4B	0.9900	O3—Co1	2.0906 (11)
C5—N1	1.4907 (17)	O3—H3	0.83 (2)
C5—C6	1.522 (2)	Co1—O2^i	2.0890 (10)
C5—H5A	0.9900	Co1—O3^i	2.0906 (11)
C5—H5B	0.9900	Co1—N1^i	2.1557 (12)
N1—C1—C2	117.02 (11)	C8—C7—H7B	109.5
N1—C1—H1A	108.0	H7A—C7—H7B	109.5
C2—C1—H1A	108.0	C8—C7—H7C	109.5
N1—C1—H1B	108.0	H7A—C7—H7C	109.5
C2—C1—H1B	108.0	H7B—C7—H7C	109.5
H1A—C1—H1B	107.3	O5—C8—O4	124.21 (14)
O1—C2—C1	112.87 (12)	O5—C8—C7	116.91 (15)
O1—C2—H2A	109.0	O4—C8—C7	118.83 (15)
C1—C2—H2A	109.0	C3—N1—C1	110.51 (11)
O1—C2—H2B	109.0	C3—N1—C5	113.40 (11)
C1—C2—H2B	109.0	C1—N1—C5	110.81 (11)
H2A—C2—H2B	107.8	C3—N1—Co1	105.10 (8)
N1—C3—C4	112.26 (12)	C1—N1—Co1	109.54 (8)
N1—C3—H3A	109.2	C5—N1—Co1	107.22 (8)
C4—C3—H3A	109.2	C2—O1—H1	109.5
N1—C3—H3B	109.2	C4—O2—Co1	114.52 (8)
C4—C3—H3B	109.2	C4—O2—H2	106.2 (13)
H3A—C3—H3B	107.9	Co1—O2—H2	116.9 (13)
O2—C4—C3	109.82 (11)	C6—O3—Co1	109.73 (9)
O2—C4—H4A	109.7	C6—O3—H3	107.0 (13)
C3—C4—H4A	109.7	Co1—O3—H3	118.2 (14)
O2—C4—H4B	109.7	O2—Co1—O2^i	180.00 (6)
C3—C4—H4B	109.7	O2—Co1—O3^i	89.67 (4)
H4A—C4—H4B	108.2	O2^i—Co1—O3^i	90.33 (4)
N1—C5—C6	112.40 (11)	O2—Co1—O3	90.33 (4)
N1—C5—H5A	109.1	O2^i—Co1—O3	89.67 (4)
C6—C5—H5A	109.1	O3^i—Co1—O3	180.00 (6)
N1—C5—H5B	109.1	O2—Co1—N1^i	98.84 (4)
C6—C5—H5B	109.1	O2^i—Co1—N1^i	81.16 (4)
H5A—C5—H5B	107.9	O3^i—Co1—N1^i	82.82 (4)
O3—C6—C5	110.46 (11)	O3—Co1—N1^i	97.18 (4)
O3—C6—H6A	109.6	O2—Co1—N1	81.16 (4)
C5—C6—H6A	109.6	O2^i—Co1—N1	98.84 (4)
O3—C6—H6B	109.6	O3^i—Co1—N1	97.18 (4)
C5—C6—H6B	109.6	O3—Co1—N1	82.82 (4)
H6A—C6—H6B	108.1	N1^i—Co1—N1	180.00 (6)
C8—C7—H7A	109.5
N1—C1—C2—O1	72.28 (16)	C4—O2—Co1—N1	−2.28 (9)
N1—C3—C4—O2	43.53 (16)	C6—O3—Co1—O2	61.46 (9)
N1—C5—C6—O3	−46.87 (16)	C6—O3—Co1—O2^i	−118.54 (9)
C4—C3—N1—C1	−161.43 (12)	C6—O3—Co1—N1^i	160.42 (9)
C4—C3—N1—C5	73.45 (14)	C6—O3—Co1—N1	−19.58 (9)
C4—C3—N1—Co1	−43.34 (13)	C3—N1—Co1—O2	24.35 (8)
C2—C1—N1—C3	−65.38 (15)	C1—N1—Co1—O2	143.09 (9)
C2—C1—N1—C5	61.20 (15)	C5—N1—Co1—O2	−96.60 (9)
C2—C1—N1—Co1	179.29 (10)	C3—N1—Co1—O2^i	−155.65 (8)
C6—C5—N1—C3	−87.33 (14)	C1—N1—Co1—O2^i	−36.91 (9)
C6—C5—N1—C1	147.71 (12)	C5—N1—Co1—O2^i	83.40 (9)
C6—C5—N1—Co1	28.21 (13)	C3—N1—Co1—O3^i	−64.19 (9)
C3—C4—O2—Co1	−20.47 (14)	C1—N1—Co1—O3^i	54.55 (9)
C5—C6—O3—Co1	40.40 (13)	C5—N1—Co1—O3^i	174.86 (8)
C4—O2—Co1—O3^i	95.04 (9)	C3—N1—Co1—O3	115.81 (9)
C4—O2—Co1—O3	−84.96 (9)	C1—N1—Co1—O3	−125.45 (9)
C4—O2—Co1—N1^i	177.72 (9)	C5—N1—Co1—O3	−5.14 (8)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4	0.83 (2)	1.77 (2)	2.5952 (16)	173.7 (19)
O2—H2···O5^i	0.85 (2)	1.71 (2)	2.5584 (15)	176.9 (19)
O1—H1···O4^ii	0.84 (2)	1.89 (2)	2.7240 (16)	176

Symmetry codes: (i) −x, −y, −z; (ii) x, −y−1/2, z+1/2.